Cheap flights from Toronto to Chicago from C$ 103

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Flight information for Toronto to Chicago
(YTO to CHI)

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago

Best price found

C$ 103

Fastest flight time

1h 35m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Toronto in the past 72 hours is C$ 103. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is C$ 319.
The fastest flight from Toronto to Chicago takes 1h 35m
Direct flights go from Toronto to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Toronto to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Toronto to Chicago?

June. The cheapest time of year to fly to Chicago from Toronto is June. The most expensive is March.

What is the cheapest day to depart Toronto for Chicago?

Thursday. The cheapest day of the week is typically Thursday. The most expensive is typically Sunday

When is the cheapest time to fly from Toronto to Chicago?

in the afternoon. Toronto to Chicago flights are approximately 18% more expensive at noon than in the afternoon

What is the cheapest airline that flies to Chicago from Toronto?

Swoop. Delta, Egypt Air, and Flair Airlines are the most popular carriers operating from Toronto to Chicago

What is the cheapest Toronto to Chicago flight route?

Toronto Island - Chicago Midway. Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices

How far in advance should you book Toronto to Chicago flights?

59 days before. The cheapest time to buy a flight from Toronto to Chicago is approximately 59 days to departure

When you’re planning your trip from Toronto to Chicago, the most popular airport-to-airport route is Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. When booking your trip to Chicago, it is helpful to have an alternative airport to fly out of. Good options for departure airports when travelling to Chicago, you can try Toronto Island Airport (in Toronto), Hamilton Airport (in Hamilton), or Toronto Kitchener-Waterloo Airport (in Toronto). If you are looking for an alternate airport to fly into near Chicago O'Hare Intl Airport, Chicago Midway Airport is a great option and is located in Chicago. The least expensive flight option from Toronto to Chicago will typically be YTZ — MDW during the month of March with an average price of C$ 235 RT.

Toronto Pearson Intl Airport (YYZ) to Chicago O'Hare Intl Airport (ORD)C$ 272
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Toronto Island Airport (YTZ) to Chicago Midway Airport (MDW)C$ 235
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Toronto Pearson Intl Airport (YYZ) to Chicago Midway Airport (MDW)C$ 314
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Toronto Island Airport (YTZ) to Chicago O'Hare Intl Airport (ORD)C$ 456
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Hamilton Airport (YHM) to Chicago O'Hare Intl Airport (ORD)C$ 584
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Toronto Kitchener-Waterloo Airport (YKF) to Chicago O'Hare Intl Airport (ORD)C$ 382
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Easily compare round-trip flights from Toronto to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Toronto to Chicago by changing tabs
Porter Airlines
10 Apr.
YTZ5:30 a.m.Toronto Island
1h 47m
MDW7:17 a.m.Chicago Midway
17 Apr.
MDW1:49 p.m.Chicago Midway
1h 42m
YTZ3:31 p.m.Toronto Island
United Airlines
14 Apr.
YYZ1:30 p.m.Toronto Pearson Intl
2h 02m
ORD3:32 p.m.Chicago O'Hare Intl
16 Apr.
ORD3:13 a.m.Chicago O'Hare Intl
1h 42m
YYZ4:55 a.m.Toronto Pearson Intl
Air Canada
8 Apr.
YYZ10:30 a.m.Toronto Pearson Intl
1h 50m
ORD12:20 p.m.Chicago O'Hare Intl
12 Apr.
ORD2:45 p.m.Chicago O'Hare Intl
1h 38m
YYZ4:23 p.m.Toronto Pearson Intl
American Airlines
8 Apr.
YYZ7:01 a.m.Toronto Pearson Intl
5h 23m
1 stop
ORD12:24 p.m.Chicago O'Hare Intl
18 Apr.
ORD1:35 a.m.Chicago O'Hare Intl
4h 45m
1 stop
YYZ6:20 a.m.Toronto Pearson Intl
ANA
20 May
YYZ5:00 a.m.Toronto Pearson Intl
1h 54m
ORD6:54 a.m.Chicago O'Hare Intl
30 May
ORD2:44 p.m.Chicago O'Hare Intl
1h 39m
YYZ4:23 p.m.Toronto Pearson Intl
Delta
17 Apr.
YYZ1:45 p.m.Toronto Pearson Intl
4h 26m
1 stop
ORD6:11 p.m.Chicago O'Hare Intl
21 Apr.
ORD10:09 a.m.Chicago O'Hare Intl
7h 23m
1 stop
YYZ5:32 p.m.Toronto Pearson Intl

Find the cheapest one-way flights from Toronto to Chicago

If you're looking for one-way flights from Toronto to Chicago, view some of our deals below provided by ANA, Air Canada and Porter Airlines
Air Canada
26 Jul.
YYZ2:30 a.m.Toronto Pearson Intl
1h 55m
ORD4:25 a.m.Chicago O'Hare Intl
Porter Airlines
23 Apr.
YTZ6:45 a.m.Toronto Island
1h 47m
MDW8:32 a.m.Chicago Midway
ANA
29 Apr.
YYZ3:00 a.m.Toronto Pearson Intl
2h 02m
ORD5:02 a.m.Chicago O'Hare Intl

Search last-minute flights to Chicago from Toronto

Find and compare round-trip flight prices for your last-minute flight from Toronto to Chicago
Multiple Airlines
26 Mar.
YKF11:45 a.m.Toronto Kitchener-Waterloo
17h 22m
1 stop
ORD5:07 a.m.Chicago O'Hare Intl
29 Mar.
ORD5:15 a.m.Chicago O'Hare Intl
13h 40m
2 stops
YKF6:55 p.m.Toronto Kitchener-Waterloo
Porter Airlines
26 Mar.
YTZ11:30 a.m.Toronto Island
1h 47m
MDW1:17 p.m.Chicago Midway
29 Mar.
MDW1:15 p.m.Chicago Midway
1h 42m
YTZ2:57 p.m.Toronto Island
Air Canada
26 Mar.
YYZ4:55 p.m.Toronto Pearson Intl
1h 50m
ORD6:45 p.m.Chicago O'Hare Intl
8 Apr.
ORD11:35 a.m.Chicago O'Hare Intl
1h 37m
YYZ1:12 p.m.Toronto Pearson Intl
American Airlines
26 Mar.
YYZ7:44 a.m.Toronto Pearson Intl
1h 57m
ORD9:41 a.m.Chicago O'Hare Intl
4 Apr.
ORD5:40 a.m.Chicago O'Hare Intl
1h 55m
YYZ7:35 a.m.Toronto Pearson Intl
Delta
22 Mar.
YYZ12:35 p.m.Toronto Pearson Intl
6h 44m
1 stop
ORD7:19 p.m.Chicago O'Hare Intl
31 Mar.
ORD3:35 a.m.Chicago O'Hare Intl
5h 02m
1 stop
YYZ8:37 a.m.Toronto Pearson Intl
United Airlines
26 Mar.
YYZ3:40 a.m.Toronto Pearson Intl
1h 50m
ORD5:30 a.m.Chicago O'Hare Intl
29 Mar.
ORD2:40 a.m.Chicago O'Hare Intl
1h 37m
YYZ4:17 a.m.Toronto Pearson Intl

Best airlines flying from Toronto to Chicago

Compare and see reviews for airlines that fly from Toronto to Chicago with momondo
AirlineRatingFree CancellationPrice
WestJetPriceFrom C$ 131Free CancellationRating
7.3
142 reviews
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DeltaPriceFrom C$ 170Free CancellationRating
7.8
772 reviews
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SwoopPriceFrom C$ 176Free CancellationRating
0.0
0 reviews
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Flair AirlinesPriceFrom C$ 189Free CancellationRating
6.1
17 reviews
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American AirlinesPriceFrom C$ 216Free CancellationRating
7.2
2,055 reviews
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Porter AirlinesPriceFrom C$ 230Free CancellationRating
8.2
53 reviews
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Air CanadaPriceFrom C$ 260Free CancellationRating
7.3
323 reviews
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United AirlinesPriceFrom C$ 283Free CancellationRating
7.2
1,656 reviews
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Air New ZealandPriceFrom C$ 291Free CancellationRating
7.7
113 reviews
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Qantas AirwaysPriceFrom C$ 310Free CancellationRating
7.2
98 reviews
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  • ANA Flights From Toronto to Chicago

    Across 15 ANA flights from Toronto to Chicago this week, the average price was C$ 295, with the best ANA deals starting from C$ 233 round-trip. 97 users have rated ANA on momondo, with an average score of 8.5/10.

  • Porter Airlines Flights From Toronto to Chicago

    Porter Airlines is also a popular choice for this route. Porter Airlines flight deals for Toronto to Chicago start from as low as C$ 168 round-trip, depending on your selected dates, with average Porter Airlines deals seen on momondo around C$ 236. Porter Airlines operates 13 flights to Chicago from Toronto in an average week. Users have rated it 8.2/10 across 53 reviews.


Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
8 Apr.
YYZ10:30 a.m.Toronto Pearson Intl
1h 50m
ORD12:20 p.m.Chicago O'Hare Intl
12 Apr.
ORD2:45 p.m.Chicago O'Hare Intl
1h 38m
YYZ4:23 p.m.Toronto Pearson Intl
Air Canada
25 May
YYZ4:00 a.m.Toronto Pearson Intl
1h 50m
ORD5:50 a.m.Chicago O'Hare Intl
8 Jun.
ORD5:15 p.m.Chicago O'Hare Intl
1h 43m
YYZ6:58 p.m.Toronto Pearson Intl
Air Canada
16 Jun.
YYZ2:30 a.m.Toronto Pearson Intl
1h 55m
ORD4:25 a.m.Chicago O'Hare Intl
18 Jun.
ORD5:15 p.m.Chicago O'Hare Intl
1h 43m
YYZ6:58 p.m.Toronto Pearson Intl

United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets
United Airlines
14 Apr.
YYZ1:30 p.m.Toronto Pearson Intl
2h 02m
ORD3:32 p.m.Chicago O'Hare Intl
16 Apr.
ORD3:13 a.m.Chicago O'Hare Intl
1h 42m
YYZ4:55 a.m.Toronto Pearson Intl
United Airlines
16 Apr.
YYZ5:15 p.m.Toronto Pearson Intl
2h 02m
ORD7:17 p.m.Chicago O'Hare Intl
18 Apr.
ORD8:45 a.m.Chicago O'Hare Intl
6h 29m
1 stop
YYZ3:14 p.m.Toronto Pearson Intl
United Airlines
14 Apr.
YYZ3:44 p.m.Toronto Pearson Intl
4h 18m
1 stop
ORD8:02 p.m.Chicago O'Hare Intl
16 Apr.
ORD3:13 a.m.Chicago O'Hare Intl
1h 42m
YYZ4:55 a.m.Toronto Pearson Intl

  • How far is Toronto to Chicago by plane?

    Chicago is 700.6 km away from Toronto. Flights usually cover this in 1h 47m, depending on flying conditions and air traffic around both airports.


If you are making a trip from to Chicago from Toronto, you will find that there are two airports in the Toronto area that offer flights to Chicago. They include Toronto Island Airport (YTZ) and Toronto Pearson International Airport (YYZ). Two airports are available in the Chicago area: Chicago O'Hare International Airport (ORD) and Chicago Midway Airport (MDW). Toronto Pearson International Airport Chicago O’Hare International Airport are the larger and busier airport options in their respective cities.

There are several options for nonstop flights between Toronto and Chicago. Porter Airlines offers a nonstop flight that travels between Toronto Island Airport and Chicago Midway Airport. Air Canada operates a nonstop flight that travels between Toronto Pearson International Airport and Chicago O'Hare International Airport. In addition, both United Airlines and American Airlines operate nonstop flights along this same route from Toronto Pearson International Airport to Chicago O'Hare International Airport.

Beyond the very convenient nonstop flights offered between these two cities, you will also find some one-stop flight options available that can save you money on your trip from Toronto to Chicago. Air Canada offers a one-stop flight with service from Toronto Island Airport to Chicago O'Hare International Airport with a layover at Montreal Pierre Elliott Trudeau International Airport (YUL) that will add about four hours to your travel time compared to the nonstop options. Air Canada also offers a one-stop flight from Toronto Pearson International Airport to Chicago O’Hare International Airport that will also add about four hours to your travel time. Delta Airlines provides a one-stop flight from Toronto Pearson International Airport to Chicago O' Hare International Airport with a layover at New York LaGuardia Airport (LGA). You will also find a one-stop flight operated by United Airlines between Toronto Pearson International Airport and Chicago O'Hare International Airport with a layover at Cleveland Hopkins International Airport (CLE).


As a Canadian citizen traveling to the United States, you will need to provide proof of Canadian citizenship upon entry into the United States. You can do this by presenting a passport, which must be valid for the entire duration of your stay. Alternatively, you can use a valid NEXUS card, which you can use at a self-service kiosk at the airport in Chicago. Most Canadian visitors will not need a visa to travel to the United States for a stay of up to six months. When you arrive in the US, you are required to declare the intended duration of your stay in the country.


Alternative routes for Toronto to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Ottawa to Chicago Flights
Fastest flight time2h 08m
Cheapest priceC$ 376
Toronto to St. Louis Flights
Fastest flight time2h 09m
Cheapest priceC$ 426
London, Ontario to Chicago Flights
Fastest flight time13h 32m
Cheapest priceC$ 522
Ottawa to St. Louis Flights
Fastest flight time4h 50m
Cheapest priceC$ 676
Sudbury, Ontario to Chicago Flights
Fastest flight time5h 32m
Cheapest priceC$ 672
Toronto to Moline Flights
Fastest flight time4h 14m
Cheapest priceC$ 628
Kingston, Ontario to Chicago Flights
Fastest flight time7h 18m
Cheapest priceC$ 1,309
Toronto to Bloomington, Illinois Flights
Fastest flight time9h 53m
Cheapest priceC$ 949
Toronto to Champaign Flights
Fastest flight time8h 43m
Cheapest priceC$ 867
Toronto to Peoria, Illinois Flights
Fastest flight time26h 29m
Cheapest priceC$ 371

Similar Toronto to Chicago flights

Flexible with your destination? Broaden your search and find flights similar to your Toronto to Chicago route

Why use momondo?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Toronto.

Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.

Of course. momondo tracks the price of Toronto to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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